KR880003912A - Process for preparing pyridine-2, 3-dicarboxylic acid - Google Patents

Process for preparing pyridine-2, 3-dicarboxylic acid Download PDF

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Publication number
KR880003912A
KR880003912A KR1019870010116A KR870010116A KR880003912A KR 880003912 A KR880003912 A KR 880003912A KR 1019870010116 A KR1019870010116 A KR 1019870010116A KR 870010116 A KR870010116 A KR 870010116A KR 880003912 A KR880003912 A KR 880003912A
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South Korea
Prior art keywords
pyridine
dicarboxylic acid
oxide
addition salt
hydroxyquinoline
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KR1019870010116A
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Korean (ko)
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KR950011411B1 (en
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프레드릭 리이커 윌리엄
앨런 대니얼즈 윌리엄
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아메리칸 사이아나밋드 캄파니
원본미기재
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

Abstract

내용 없음No content

Description

피리딘-2, 3-디카르복실산의 제조 방법Process for preparing pyridine-2, 3-dicarboxylic acid

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (10)

하기식 (Ⅱ)의 치환 퀴놀린을 수성 염기내에서 과산화수소로 산화시키는 것으로 구성된 하기식(Ⅰ)의 비치환 및 치환 피리딘-2, 3-디카르복실산 또는 그 N-옥사이드 또는 그산부가염을 제조하는 방법.To prepare an unsubstituted and substituted pyridine-2,3-dicarboxylic acid or an N-oxide or acid addition salt thereof of formula (I) consisting of oxidizing substituted quinoline of formula (II) with hydrogen peroxide in an aqueous base. How to. 상기식에서, R1,R2및 R3는 각각 수소, C1-C6알킬, 히드록시-C1-C6알킬, C1-C6알콕시, 페녹시, C1-C4할로알킬, 니트로, 히드록시, 아미노, C1-C4알킬아미노, 디저급알킬아미노 또는 C1-C4알킬아미노, 디저급알킬아미노 또는 C1-C4알킬설포닐기, 카르복시, 아실, 아미도;또는 하나의 C1-C4알킬, C1-C4알콕시 또는 할로겐으로 임의적으로 치환된 페닐;디플루오로 메톡시, 트리플루오로메톡시, 1,1,2,2-테트라플루오로 에톡시, 하나 또는 세개의 할로겐으로 임의로 치환된 C3-C8직쇄 또는 측쇄 알케닐옥시 또는 하나 또는 세개의 할로겐으로 임의로 치환된 C3-C8직쇄 또는 측쇄 알키닐옥시이고; 함께 취해질 때 R2와 R3는 임의로 치환되는 고리 YZ를 형성할 수 있고 여기서 YZ는 Q가 산호, 황 또는 질소인-(CH2)2-Q-또는-(CH)2-Q-이며, R1은 단지 수소 이고; X1,X2,X3및 X4는 각각 수소, 히드록시, SO3H, SO2Cl, SH, Cl, F, Br, I,CO2H, NO2, NH2또는 NHR, NR2, CONR2또는 COR(여기서 R은 C1-C4알킬이다)이고, 단 X1, X2, X3또는 X4중 하나는 수소가 아니다.Wherein R 1 , R 2 and R 3 are each hydrogen, C 1 -C 6 alkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, C 1 -C 4 haloalkyl, Nitro, hydroxy, amino, C 1 -C 4 alkylamino, loweralkylamino or C 1 -C 4 alkylamino, diloweralkylamino or C 1 -C 4 alkylsulfonyl groups, carboxy, acyl, amido; or Phenyl optionally substituted with one C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; difluoro methoxy, trifluoromethoxy, 1,1,2,2-tetrafluoro ethoxy, one Or C 3 -C 8 straight or branched chain alkenyloxy optionally substituted with three halogens or C 3 -C 8 straight or branched chain alkynyloxy optionally substituted with one or three halogens; When taken together R 2 and R 3 may form an optionally substituted ring YZ, wherein YZ is — (CH 2 ) 2 —Q—or — (CH) 2 —Q—, wherein Q is coral, sulfur or nitrogen, R 1 is only hydrogen; X 1 , X 2 , X 3 and X 4 are hydrogen, hydroxy, SO 3 H, SO 2 Cl, SH, Cl, F, Br, I, CO 2 H, NO 2 , NH 2 or NHR, NR 2 , CONR 2 or COR, where R is C 1 -C 4 alkyl, provided that one of X 1 , X 2 , X 3 or X 4 is not hydrogen. 제1항에 있어서, 과산화수소 약 8-20몰 당량을 약 75℃-90℃의 온도에서 1몰 당량의 수성 염기 소량 내식(Ⅱ)의 퀴놀린의 휘저어 섞은 용액에 첨가하는 방법.The method of claim 1, wherein about 8-20 molar equivalents of hydrogen peroxide are added to a stirred solution of quinoline of 1 molar equivalent of aqueous base small amount of corrosion resistant formula (II) at a temperature of about 75 ° C.-90 ° C. 7. 제2항에 있어서, 퀴놀린을 중량 기준으로 약 15%-35%농도의 수성염기 4-7몰 당량에 용해시키는 방법.The method of claim 2 wherein the quinoline is dissolved in 4-7 molar equivalents of aqueous base at about 15% -35% concentration by weight. 제3항에 있어서, 염기가 수산화 칼륨 또는 수산화나트륨인 방법.The method of claim 3 wherein the base is potassium hydroxide or sodium hydroxide. 제4항에 있어서, X1이 히드록시, Cl,F,Br,I,CO2H,NO2,SO3H,SO2Cl,SH,NH2,NHR,The compound of claim 4, wherein X 1 is hydroxy, Cl, F, Br, I, CO 2 H, NO 2 , SO 3 H, SO 2 Cl, SH, NH 2 , NHR, NR2,CONR2,COR(여기서 R은 C1-C4알킬 또는 수소이다)인 4-치환, 5-치환, 6-치환, 4,5-이치환, 4,6이치환 및 5,6-이치환-알킬피리딘-2,3-디카르복실산, 그 N-옥사이드의 제조방법.4-substituted, 5-substituted, 6-substituted, 4,5-disubstituted, 4,6-disubstituted and 5,6-disubstituted, which are NR 2 , CONR 2 , COR, wherein R is C 1 -C 4 alkyl or hydrogen -Alkylpyridine-2,3-dicarboxylic acid, method for producing N-oxide thereof. 제5항에 있어서, 3-에틸-8-히드록시퀴놀린 또는 그 산부가염으로부터 5-에틸-피리딘-2,3-디카르복실산을 제조하는 방법.The process according to claim 5, wherein 5-ethyl-pyridine-2,3-dicarboxylic acid is prepared from 3-ethyl-8-hydroxyquinoline or an acid addition salt thereof. 제5항에 있어서, 3-메틸-8-히드록시퀴놀린 또는 그 산부가염으로부터 5-메틸-피리딘-2,3-디카르복실산을 제조하는 방법.The process according to claim 5, wherein 5-methyl-pyridine-2,3-dicarboxylic acid is prepared from 3-methyl-8-hydroxyquinoline or an acid addition salt thereof. 제4항에 있어서, 8-히드록시키놀린 또는 그의 산부가염으로부터 피리딘-2,3-디카르복실산과 8-히드록시키놀린 N-옥사이드 또는 그 부가염으로부터 피리딘-2,3-디카르복실산 N-옥사이드를 제조하는 방법.The pyridine-2,3-dicarboxylic acid according to claim 4, wherein the pyridine-2,3-dicarboxylic acid from 8-hydroxyquinoline or an acid addition salt thereof and pyridine-2,3-dicarboxyl from 8-hydroxyquinoline N-oxide or an addition salt thereof Process for preparing acid N-oxide. 제5항에 있어서, 3-에틸-8-히드록시퀴놀린-N-옥사이드 또는 그 부가염으로부터 5-에틸-피리딘-2,3-디카르복실산 N-옥사이드를 제조하는 방법.The process according to claim 5, wherein 5-ethyl-pyridine-2,3-dicarboxylic acid N-oxide is prepared from 3-ethyl-8-hydroxyquinoline-N-oxide or an addition salt thereof. 제5항에 있어서, 3-메틸-8-히드록시퀴놀린-N-옥사이드 또는 그 부가염으로부터 5-메틸-피리딘-2,3-디카르복실산 N-옥사이드를 제조하는 방법.The process of claim 5, wherein 5-methyl-pyridine-2,3-dicarboxylic acid N-oxide is prepared from 3-methyl-8-hydroxyquinoline-N-oxide or an addition salt thereof. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019870010116A 1986-09-12 1987-09-11 Method for the preparation of pyridine-2,3-dicarboxylic acids KR950011411B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US90671386A 1986-09-12 1986-09-12
US906713 1986-09-12
US06/906,713 1986-09-12

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KR880003912A true KR880003912A (en) 1988-06-01
KR950011411B1 KR950011411B1 (en) 1995-10-04

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EP (1) EP0259687B1 (en)
JP (1) JPH07116153B2 (en)
KR (1) KR950011411B1 (en)
AR (1) AR245697A1 (en)
AU (1) AU599698B2 (en)
BR (1) BR8704717A (en)
CA (1) CA1297112C (en)
CS (1) CS270573B2 (en)
DD (1) DD262227A5 (en)
DE (1) DE3771153D1 (en)
DK (1) DK169518B1 (en)
ES (1) ES2028834T3 (en)
GR (1) GR3001297T3 (en)
HU (1) HU203535B (en)
IE (1) IE59547B1 (en)
IL (1) IL83795A (en)
SU (1) SU1690543A3 (en)
ZA (1) ZA876838B (en)

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* Cited by examiner, † Cited by third party
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US5565412A (en) * 1984-05-21 1996-10-15 American Cyanamid Co. (2-imidazolin-2-yl) fused heteropyridine compounds, intermediates for the preparation of and use of said compounds as herbicidal agents
US5252538A (en) * 1984-05-21 1993-10-12 American Cyanamid Company (2-imidazolin-2-yl) fused heteropyridine compounds, intermediates for the preparation of and use of said compounds as herbicidal agents
IL89142A (en) * 1988-03-10 1993-04-04 American Cyanamid Co Method for the sequential oxidation of substituted 8-hydroxyquinolines to produce substituted pyridine-2,3- dicarboxylic acids
ES2058625T3 (en) * 1989-03-22 1994-11-01 American Cyanamid Co METHOD FOR SEQUENTIAL OXIDATION OF SUBSTITUTED QUINOLINS TO PRODUCE SUBSTITUTED PIRIDIN-2,3-DICARBOXYLIC ACIDS.
TW232013B (en) * 1992-04-24 1994-10-11 Takeda Pharm Industry Co Ltd
NZ314904A (en) * 1996-06-10 1998-06-26 American Cyanamid Co Preparation of a herbicidal [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halide

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JPS56118067A (en) * 1980-02-25 1981-09-16 Yamamoto Kagaku Gosei Kk Preparation of copper quinolinate

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CS652987A2 (en) 1989-11-14
IL83795A (en) 1992-06-21
AU599698B2 (en) 1990-07-26
DK169518B1 (en) 1994-11-21
DK475387D0 (en) 1987-09-11
DD262227A5 (en) 1988-11-23
JPS63119466A (en) 1988-05-24
ES2028834T3 (en) 1992-07-16
EP0259687A2 (en) 1988-03-16
CS270573B2 (en) 1990-07-12
CA1297112C (en) 1992-03-10
GR3001297T3 (en) 1992-08-26
JPH07116153B2 (en) 1995-12-13
HU203535B (en) 1991-08-28
AU7828287A (en) 1988-03-17
DK475387A (en) 1988-03-13
EP0259687A3 (en) 1989-05-31
AR245697A1 (en) 1994-02-28
IE59547B1 (en) 1994-03-09
DE3771153D1 (en) 1991-08-08
BR8704717A (en) 1988-05-03
IL83795A0 (en) 1988-02-29
SU1690543A3 (en) 1991-11-07
EP0259687B1 (en) 1991-07-03
ZA876838B (en) 1988-03-15
KR950011411B1 (en) 1995-10-04
IE872437L (en) 1988-03-12
HUT48211A (en) 1989-05-29

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